Today we’d like to introduce you to Stacey Bailey.
Hi Stacey, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
My journey began in Charleston in 2004, where I moved to attend the College of Charleston (CofC). Beyond earning a degree in Arts Management, I made lifelong connections while helping to launch the first iteration of the women’s ultimate frisbee team—a foundation that taught me about teamwork and building something from the ground up.
Building a Career in Operations
After graduation, I found myself drawn to the world of marketing and digital agencies. Here, I quickly discovered a natural aptitude for project management and operations, thriving on structure and efficiency. This led to a 12-year tenure at a digital agency, culminating in serving as Chief Operating Officer (COO) for the last four years.
This period was defined by leading through complexity: I successfully navigated an international merger, a complete rebrand, and the challenges of the global pandemic, all while balancing professional demands with raising two young children at home. My operational experience is rooted in real-world, high-stakes leadership.
Transition to Purpose-Driven Consulting
In 2023, I intentionally chose to reset my focus. This pivotal moment included a 100-day journey of traveling and connecting with my family, which allowed me to align my passion with my professional path.
Today, I leverage my COO experience to help entrepreneurs and organizational leaders develop healthy, sustainable leadership practices. My current work centers on enabling businesses to scale effectively by placing vision, values, and ethos at the core of their strategy.
Community and Creative Engagement
My commitment extends into the community, where I believe healthy leaders and intentional strategies can change our communities. I’ve been recognized as a 40 Under 40 by the SC Business Journal (2020) and a Best and Brightest with the Cystic Fibrosis Foundation (2013). I actively serve on two city commissions and hold board positions for organizations like Meet Us on the Frontlines, Be the Ones, and Friends of James Simons Montessori.
Finally, I have maintained my creative edge as a resident improviser at Theatre 99 since 2012, a practice that continually sharpens my skills in collaboration, quick-thinking, and empathetic communication.
We all face challenges, but looking back would you describe it as a relatively smooth road?
First and foremost, I lost my mother when I was 18. That kind of early loss shakes your foundation and forced me to mature quickly. It instilled a deep, almost instinctual drive in me to create stability and structure, which is exactly why I thrived in operations—I was always trying to build a strong, healthy system. It also taught me the non-negotiable value of being intentional with my time and energy.
Professionally, the biggest struggles were managing that constant high-stakes complexity. Leading through that international merger and then immediately tackling the chaos of the pandemic as a COO was relentless. It wasn’t just about the business strategy; it was about managing change fatigue across the team while trying to maintain my own personal resilience.
Finally, the struggle of the work-life juggle was very real. I was determined to be a present executive and a present mom. That meant learning to delegate effectively and realizing that the most courageous decision could be the one to press pause—which led to my sabbatical. Transitioning from the structure of a major executive role to building a consulting practice from scratch also required immense patience, learning to measure success not just by volume, but by the depth of impact.
It’s these experiences—from early loss to high-level strategy and everything in between—that have made me the resilient, values-driven leader I am today.
Thanks – so what else should our readers know about Stacey Bailey Consulting?
Stacey Bailey Consulting launched in 2025 to focus on bringing high-level executive and operational support directly to leaders, particularly here in Charleston.
Our Focus: Strategy, Accountability, and Healthy Leadership
We predominantly serve creative service leaders and nonprofit executives—people who are passionate about their mission but often need expert operational guidance to scale sustainably.
We focus on three key areas:
Strategic Planning: Helping leaders define clear, actionable, and values-aligned goals for their organizations.
Accountability: Establishing systems and routines that ensure those goals move from paper to reality.
Healthy Leadership Coaching: Working with leaders one-on-one to develop sustainable habits, reduce burnout, and foster an organizational culture that thrives.
What Sets Us Apart? Humor and Reliability
What truly sets us apart is our approach, which is grounded in two core values: Humor and Reliability.
We believe complex challenges don’t have to be tackled with dread. My background as a resident improviser at Theatre 99 since 2012 isn’t just a fun hobby—it’s a tool. It allows me to build trust quickly, thread complex ideas into a single source of truth, and ensure our work is fun, collaborative, and deeply human.
You know that when you work with us, the strategy we create will be dependable and the process to get there will be engaging and insightful.
Brand Pride and Key Offerings
I am genuinely most proud of the fact that we got started! Taking the leap to focus entirely on purpose-driven consulting after a long executive career was a major step.
Our newest offering that I’m particularly excited about is our One-Day Strategic Planning Sessions – Level Up Retreats. These sessions are designed to bring entrepreneurs and small teams together for an intensive, intentional day where they can step away from the daily grind and plan their entire year and quarters with fresh eyes and inspiration from a collaborative group. Our next one is January 21, 2026.
What We Want You to Know
If there’s one thing I want readers to know, it’s this: You do not need to navigate the complexities, uncertainties, and scaling challenges of entrepreneurship alone.
Having insightful collaboration and guidance from someone who has successfully been in the operational trenches—who has executed international mergers, managed crises, and built healthy cultures—can be immensely rewarding. We provide the expertise you need and the reliable, humorous support you deserve to move your mission forward.
What are your plans for the future?
My future plans are centered on deepening the impact of Stacey Bailey Consulting here in the local Charleston community and achieving a state of optimal flow in my work.
Focusing on Flow and Impact in 2026
First and foremost, 2026 is the year of establishing flow. This means moving beyond the initial build-out phase of the business and dedicating my energy entirely to my unique genius—the work that is most impactful for my clients. I am intentionally creating systems to ensure I can operate free from distractions, allowing me to stick to the strategic and coaching practices that move the needle for creative service and nonprofit leaders. This is about maximizing quality over quantity.
Building Sustainable Cohorts
I’m most looking forward to establishing recurring cohorts for local entrepreneurs.
I recognize that while one-on-one coaching and tailored consulting are vital, there is immense power in shared learning and community. These cohorts will provide local leaders with a structured, reliable environment to:
Plan Sustainably: Dedicate time and resources to long-term planning, rather than just reacting to daily demands.
Share Inspiration and Accountability: Benefit from peer support and guidance, ensuring they build their businesses with both intention and resilience.
No More Big Changes, Just Deepening the Work
After the transition from COO to consultant and the family sabbatical, the big changes are behind me. The focus now is entirely on deepening the existing practice—refining our services, scaling our community impact through the cohorts, and delivering the highest level of reliable, humor-infused strategic coaching that my clients expect.
Pricing:
- Full day strategy sessions $6000
- 1:1 Coaching $400/mo
- Level Up Retreat: $500/entrepreneur
Contact Info:
- Website: https://stacey-bailey.com
- Instagram: @stacey.l.bailey
- LinkedIn: https://www.linkedin.com/in/staceylbailey/
